Amplified: Whoever then breaks or does away with or relaxes one of the least [important] of these commandments and teaches men so shall be called least [important] in the kingdom of heaven, but he who practices them and teaches others to do so shall be called great in the kingdom of heaven. (Amplified Bible - Lockman)

KJV: Whosoever therefore shall break one of these least commandments, and shall teach men so, he shall be called the least in the kingdom of heaven: but whosoever shall do and teach them, the same shall be called great in the kingdom of heaven.

NLT: So if you break the smallest commandment and teach others to do the same, you will be the least in the Kingdom of Heaven. But anyone who obeys God's laws and teaches them will be great in the Kingdom of Heaven. (NLT - Tyndale House)

Philips: This means that whoever now relaxes one of the least of these commandments and teaches men to do the same will himself be called least in Heaven. But whoever teaches and practises them will be called great in the kingdom of Heaven. (New Testament in Modern English)

Wuest: Whoever therefore shall deprive of authority one of these least commandments and shall teach men so, shall be called least in the kingdom of heaven. But whoever shall do and teach them, this man shall be called great in the kingdom of heaven. (Eerdmans)

Young's Literal: 'Whoever therefore may loose one of these commands -- the least -- and may teach men so, least he shall be called in the reign of the heavens, but whoever may do and may teach them, he shall be called great in the reign of the heavens.

Charles Simeon - IT must be confessed, that amongst those who profess a high regard for the Gospel, there are some who speak of it in terms, which, to say the least, have an antinomian and licentious aspect. In their zeal against self-righteousness, they are apt to represent the law as altogether abolished: knowing that we are no longer under the law as a covenant, they express themselves as if we were freed from it also as a rule of life. But we must never forget that the Gospel is a “doctrine according to godliness;” and that “the law, so far from being made void through faith, is established by it.” In the words preceding the text, our blessed Lord had said, that “he came not to destroy the law and the prophets, but to fulfil them: and in the words before us, he teaches us to infer from thence the undiminished authority of the sacred code. (Read the entire sermon - Matthew 5:19 The Danger of Little Sins)

Whoever then - This phrase refers back to what Jesus had just declared regarding the Law. This section emphasizes that God’s law is a reflection of God’s holy, righteous and good character (Ro 7:12) and is therefore changeless and eternal.

Annuls (3089) (luo cf the compound kataluo = abolish, used by Jesus in Mt 5:17 [note]) means to break, set loose, release, dissolve, or even to melt. The idea is that of reducing God's Law to nothing, making it inoperative, in essence by loosing ourselves from its requirements and standards.

Least (1646) (elachistos is the superlative of mikrós = small) means the least, minimal in magnitude, number and quantity. Jesus' point is that in fact some of God's commandments are greater than others, but irregardless they are all holy and all important and are not to be disregarded. Jesus declares that He will hold those in lowest esteem who hold His Word in lowest esteem. There are no insignificant or non-inspired statements in the Bible.

The commandments are, first of all, prescriptions, or directions of God, concerning particular matters, which He wanted observed with reference to circumstances as they arose, in a period when He spake immediately and with greater frequency than afterward. They were numerous, minute, and regarded as coordinate and independent of each other. In the Ten Commandments, or, more properly, Ten Words, EVm (debharim), they are reduced to a few all-comprehensive precepts of permanent validity, upon which every duty required of man is based. Certain prescriptions of temporary force, as those of the ceremonial and forensic laws, are applications of these "Words" to transient circumstances, and, for the time for which they were enacted, demanded perfect and unconditional obedience. The Psalms, and especially Ps 119, show that even under the Old Testament, there was a deep spiritual appreciation of these commandments, and the extent to which obedience was deemed a privilege rather than a mere matter of constrained external compliance with duty. In the New Testament, Jesus shows in Mt 22:37,40; Mk 12:29,31; Lk 10:27 (compare Ro 13:8,10) their organic unity. The "Ten" are reduced to two, and these two to one principle, that of love. In love, obedience begins, and works from within outward. Under the New Testament the commandments are kept when they are written upon the heart (Heb 10:16). While in the Synoptics they are referred to in a more abstract and distant way, in both the Gospel and the Epistles of John their relation to Jesus is most prominent. They are "my commandments" (Jn 14:15,21; 15:10,12); "my Father's" (Jn 10:18; 15:10); or, many times throughout the epp., "His (i.e. Christ's) commandments." The new life in Christ enkindles love, and not only makes the commandments the rule of life, but the life itself the free expression of the commandments and of the nature of God, in which the commandments are grounded. Occasionally the word is used in the singular collectively (Ex 24:12; Ps 119:96; 1 Cor 14:37). (Commandments)

Keeps and teaches - Spurgeon comments on this phrase noting that "It is vain to teach the commandments without first doing them. The doing must always precede the teaching. If a man’s example cannot be safely followed, it will be unsafe to trust his words."

Teaches (1321) (didasko [word study] from dáo= know or teach; English = didactic; see study of related noun didaskalia and the adjective didaktikos) means to provide instruction or information in a formal or informal setting. In the 97 NT uses of didasko the meaning is virtually always to teach or instruct, although the purpose and content of the teaching must be determined from the context. Didasko refers to imparting positive truth. It means to hold discourse with others in order to instruct them.

John MacArthur writes that didasko

refers to the passing on of information-often, but not necessarily, in a formal setting. It focused on content, with the purpose of discovering the truth-contrary to the forums so popular among Greeks, where discussion and the bantering about of various ideas and opinions was the primary concern (see Acts 17:21). Synagogue teaching, as illustrated by that of Jesus, was basically expository. Scripture was read and explained section by section, often verse by verse. (MacArthur, J: Matthew 1-7 Chicago: Moody PressorLogos)

How do we know that some of God's laws are "weightier" ("the least of") than others ?

Matthew records the following examples…

Teacher, which is the great commandment in the Law?" 37 And He said to him, "'YOU SHALL LOVE THE LORD YOUR GOD WITH ALL YOUR HEART, AND WITH ALL YOUR SOUL, AND WITH ALL YOUR MIND.' 38 "This is the great and foremost commandment. 39 "The second is like it, 'YOU SHALL LOVE YOUR NEIGHBOR AS YOURSELF.' 40 On these two commandments depend the whole Law and the Prophets. (Mt 23:36-40)

Woe to you, scribes and Pharisees, hypocrites! For you tithe mint and dill and cummin, and have neglected the weightier provisions of the law: justice and mercy and faithfulness; but these are the things you should have done without neglecting the others. (Mt 23:23)

What happens to those who reduce the Law (even the least of the commandments) to nothing and teach others to do the same? Will they lose their salvation? Clearly they are those who are in the "kingdom of heaven" and therefore they are believers. So Jesus is not saying one can lose his or her salvation. What He is alluding to, is the fact that one can receive a lesser reward in heaven (cf 1Cor 3:10-15, 2Cor 5:10) based upon how one handles the commandments of God - Do you esteem them highly or take them lightly, as shown by your thoughts, words and deeds? You are no longer under the law (Ro 6:14-note, Gal 5:18-Galatians 5:18 ) under grace and subject to the law of liberty (James 1:25). And yet liberty does not equate with licentiousness (cf Ro 6:1, 2, 3, 4- see notesRomans 6:1; 6:2;6:3; 6:4) (which would be the equivalent of "annulling" the commandments, of not keeping them).

John has a parallel warning in his second epistle writing…

Watch yourselves (present imperative demands a continual personal vigilance, not others but yourself!), that you might not lose what we have accomplished, but that you may receive a full reward (knowledge that rewards worked for can be lost should promote faithful, loving obedience). (2John 1:8)

Therefore do not go on passing judgment before the time, but wait until the Lord comes who will both bring to light the things hidden in the darkness and disclose the motives of men's hearts (This warning indicates that motives for service and ministry will be clear to God and a major factor in His judgment); and then each man's praise (literally "his praise") will come to him from God. (1Cor 4:5)

James gives a special warning to those who are formal teachers of God's Word…

Let not many of you become teachers, my brethren, knowing that as such we shall incur a stricter (greater - this adjective supports the idea of degrees of treatment at the judgment) judgment (the responsibility of teaching others the word of God is an awesome task that should not be accepted without prayerful consideration) (James 3:1)

MacDonald comments…

that Jesus anticipated a natural tendency to relax God’s commandments. Because they are of such a supernatural nature, people tend to explain them away, to rationalize their meaning. But whoever breaks one part of the law, and teaches other people to do the same, shall be called least in the kingdom of heaven. The wonder is that such people are permitted in the kingdom at all—but then, entrance into the kingdom is by faith in Christ. A person’s position in the kingdom is determined by his obedience and faithfulness while on earth. The person who obeys the law of the kingdom—that person shall be called great in the kingdom of heaven. (MacDonald, W., & Farstad, A. Believer's Bible Commentary)

But - Don't forget to pause and ponder term of contrast. What is the change of direction? What is the writer contrasting? Why?, etc.

The two ways one can rightly (or wrongly) handle the Word of God are by doing and teaching. Citizens of the Kingdom of Heaven should live like that is where they are going and should uphold every part of God’s law, both in their living and in their teaching…

For our citizenship is in heaven, from which also we eagerly wait for a Savior, the Lord Jesus Christ (Php 3:20-note) (What we are "waiting for" [or "looking expectantly for"] should determine what [Who] we are living for!)

At the end of Jesus' great commission, He emphasizes that in going forth and making disciples we are to be…

teaching them to observe all that I commanded you; and lo, I am with you always, even to the end of the age." (Mt 28:20)

In his letter to the Roman saints, Paul explained their relationship to the Law instructing them to…

Owe nothing to anyone except to love one another; for he who loves his neighbor has fulfilled the law. For this, "YOU SHALL NOT COMMIT ADULTERY, YOU SHALL NOT MURDER, YOU SHALL NOT STEAL, YOU SHALL NOT COVET," and if there is any other commandment, it is summed up in this saying, "YOU SHALL LOVE YOUR NEIGHBOR AS YOURSELF." Love does no wrong to a neighbor; love therefore is the fulfillment of the law. (Ro 13:8, 9, 10-see notes Ro 13:8-9;10)

Writing to the saints in Galatia (who were being tempted to keep the Law as a means of being "better Christians" or to make themselves more acceptable to God) Paul reminds them that…

you were called to freedom, brethren; only do not turn your freedom into an opportunity for the flesh (i.e., licentiousness), but through love serve one another for the whole Law is fulfilled in one word, in the statement, "YOU SHALL LOVE YOUR NEIGHBOR AS YOURSELF." But if you bite and devour one another, take care lest you be consumed by one another. But I say, walk by the Spirit, and you will not carry out the desire of the flesh. For the flesh sets its desire against the Spirit, and the Spirit against the flesh; for these are in opposition to one another, so that you may not do the things that you please. But if you are led by the Spirit, you are not under the Law (The ritual or ceremonial law - sacrifices, feasts, keeping of days, etc - has been fulfilled in Christ and are no longer to be kept under grace. The moral law remains in place and are meant for our good and to promote holiness. Their pull under the leading of the Holy Spirit draws us into true freedom. To return to a ritualistic expression of the Law enslaves us. The Holy Spirit will guide us in the path of love to fulfill the law). (Galatians 5:13-24)

In a parallel passage in Paul's letter to the Thessalonians presents his example of right doing of the Word…

You are witnesses, and so is God, how devoutly and uprightly and blamelessly we behaved toward you believers just as you know how we were exhorting and encouraging and imploring each one of you as a father would his own children, so that you may walk in a manner worthy of the God who calls you into His own kingdom and glory. (see notes1Thessalonians 2:10; 2:11; 2:12)

Greatness in the Kingdom of heaven will not be based on one's gifts but upon how one handles the word of God. And although not everyone has a formal teaching gift, every believer teaches in one way or another but the life and their actions.

John MacArthur echoes this thought commenting that "Greatness is not determined by gifts, success, popularity, reputation, or size of ministry-but by a believer’s view of Scripture as revealed in his life and teaching. Jesus’ promise is not simply to great teachers such as Paul or Augustine, Calvin, Luther, Wesley, or Spurgeon. His promise applies to every believer who teaches others to obey God’s Word by faithfully, carefully, and lovingly living by and speaking of that Word. Every believer does not have the gift of teaching the deep doctrines of Scripture, but every believer is called and is able to teach the right attitude toward it. (MacArthur, J: Matthew 1-7 Macarthur New Testament Commentary Chicago: Moody Press)

Kingdom (932) (basileia from basileus = a sovereign, king, monarch) denotes sovereignty, royal power, dominion and refers therefore to the territory or people over whom a king rules. The Kingdom of Heaven/God is the sphere in which God is acknowledged as King (In hearts giving Him obedience). In this sense (and as elaborated on below) the Kingdom has a spiritual aspect, a present physical aspect, and a future eternal aspect (beginning with the millennium, cf Mt 25:31,34), all of course depending on the context of the passage in which basileia is found. Paul is careful to remind us that the Kingdom of Heaven/God is not in observance of ordinances, external and material, but in the deeper matters of the heart, which are spiritual and essential (see note Romans 14:17)

The ‘kingdom of heaven’ is the rule of God through Christ. It is present wherever wills bow to Him. It is future, as to complete realisation, in the heaven from which it comes, and to which, like its King, it belongs even while on earth. Obviously, its subjects can only be those who feel their dependence, and in poverty of spirit have cast off self-will and self-reliance. ‘Theirs is the kingdom’ does not mean ‘they shall rule,’ but ‘of them shall be its subjects.’ True, they shall rule in the perfected form of it; but the first, and in a real sense the only, blessedness is to obey God; and that blessedness can only come when we have learned poverty of spirit, because we see ourselves as in need of all things. (entiresermon)

D Martyn Lloyd-Jones explains the kingdom of heaven as follows..

You will find certain people saying that there is a difference between the 'kingdom of heaven' and the 'kingdom of God'; but my difficulty is to know what the difference is. Why does Matthew talk about the kingdom of heaven rather than the kingdom of God? Surely the answer is that he was writing primarily for the Jews, and to the Jews, and his chief object, perhaps, was to correct the Jewish conception of the kingdom of God or the kingdom of heaven. They had got into this materialistic way of looking at the kingdom; they were thinking of it politically and in a military sense, and our Lord's whole object here is to show that His kingdom is primarily a spiritual one. In other words He says to them, 'You must not think of this kingdom primarily as anything earthly. It is a kingdom in the heavens, which is certainly going to affect the earth in many different ways, but it is essentially spiritual. It belongs to the heavenly rather than to the earthly and human sphere.'

What is this kingdom, then? It means, in its essence, Christ's rule or the sphere and realm in which He is reigning. It can be considered in three ways as follows. Many times when He was here in the days of His flesh our Lord said that the kingdom of heaven was already present. Wherever He was present and exercising authority, the kingdom of heaven was there. You remember how on one occasion, when they charged Him with casting out devils by the power of Beelzebub, He showed them the utter folly of that, and then went on to say, 'If I cast out devils by the Spirit of God, then the kingdom of God is come unto you' (Matt 12:28). Here is the kingdom of God. His authority, His reign was actually in practice. Then there is His phrase when He said to the Pharisees, 'the kingdom of God is within you, or, 'the kingdom of God is among you' (NAS "is in your midst" Luke 17:21). It was as though He were saying, 'It is being manifested in your midst. Don't say "look here" or "look there". Get rid of this materialistic view. I am here amongst you; I am doing things. It is here.' Wherever the reign of Christ is being manifested, the kingdom of God is there. And when He sent out His disciples to preach, He told them to tell the cities which received them not, 'Be ye sure of this, that the kingdom of God is come nigh unto you.' (Luke 10:9, 11, cf Luke 19:11, 21:31)

It means that; but it also means that the kingdom of God is present at this moment in all who are true believers… In writing to the Colossians he gives thanks to the Father 'who hath delivered us from the power of darkness, and hath translated us into the kingdom of his dear Son' (see note Colossians 1:13). The 'kingdom of his dear Son' is 'the kingdom of God, it is 'the kingdom of heaven', it is this new kingdom into which we have entered. Or, again, in his letter to the Philippians he says, 'Our conversation is in heaven,' or, `Our citizenship is in heaven.' We are here on earth, we obey the powers that be, we live our lives in this way. Yes; but 'our citizenship is in heaven; from whence also we wait for a Saviour' (see note Philippians 3:20). We who recognize Christ as our Lord, and in whose lives He is reigning and ruling at this moment, are in the kingdom of heaven and the kingdom of heaven is in us. We have been translated into the 'kingdom of his dear Son'; we have become a 'kingdom of priests. (cf 1Pe 2:9, 10-notes1Pe 2:9; 10, Re 1:6-note, Re 5:10-note)

The third and last way of looking at the kingdom is this. There is a sense in which it is yet to come. It has come; it is coming; it is to come. It was here when He was exercising authority; it is here in us now; and yet it is to come. It will come when this rule and reign of Christ will be established over the whole world even in a physical and material sense. The day is coming when the kingdoms of this world will have become 'the kingdoms of our Lord, and of his Christ, when Jesus shall reign where'er the sun Doth his successive journeys run; His kingdom stretch from shore to shore, Till moons shall wax and wane no more. (Play Isaac Watts precious hymn - Jesus Shall Reign sing it out unto the Lord - Vocal Version)

It will then have come, completely and entirely, and everything will be under His dominion and sway. Evil and Satan will be entirely removed; there will be `new heavens and a new earth, wherein dwelleth righteousness' (2Pe 3:13-note), and then the kingdom of heaven will have come in that material way. The spiri­tual and the material will become one in a sense, and all things will be subject to His sway, that 'at the name of Jesus every knee should bow, of things in heaven, and things in earth, and things under the earth; and that every tongue should confess that Jesus Christ is Lord, to the glory of God the Father' (Php 2:10, 11-notes). (Lloyd-Jones, D. M. Studies in the Sermon on the Mount) (Bolding added)

Amplified: For I tell you, unless your righteousness (your uprightness and your right standing with God) is more than that of the scribes and Pharisees, you will never enter the kingdom of heaven. (Amplified Bible - Lockman)

KJV: For I say unto you, That except your righteousness shall exceed the righteousness of the scribes and Pharisees, ye shall in no case enter into the kingdom of heaven

NLT: "But I warn you—unless you obey God better than the teachers of religious law and the Pharisees do, you can't enter the Kingdom of Heaven at all! (NLT - Tyndale House)

Philips: For I tell you that your goodness must be a far better thing then the goodness of the scribes and Pharisees before you can set foot in the kingdom of Heaven at all! (New Testament in Modern English)

Wuest: For I am saying to you, unless your righteousness excels that of the men learned in the sacred scriptures and that of the Pharisees, not in any case will you enter the kingdom of heaven. (Wuest: Expanded Translation: Eerdmans)

Young's Literal: 'For I say to you, that if your righteousness may not abound above that of the scribes and Pharisees, ye may not enter to the reign of the heavens.

Charles Simeon - IT would be a gratification to many to know the lowest degree of piety that would suffice for their admission into the kingdom of heaven. But to have such a line drawn for us, would be by no means profitable: for it may well be doubted, whether any, who under present circumstances are slothful in their pursuit of holiness, would be quickened by it; and there is reason to fear that the zeal of many would be damped. Information, however, of a nature not very dissimilar, is given us; and it will be found of the highest importance to every child of man. Our blessed Lord has marked out for us a line, that must be passed by all who would be numbered amongst his true disciples. There were certain characters, very numerous among the Jews, characters much contemplated and much admired; these, he tells us, must be surpassed. To equal the most exalted among them will not suffice: our righteousness must exceed theirs, if ever we would enter into the kingdom of heaven. The persons we refer to were the Scribes and Pharisees; the former of whom were the learned teachers and expositors of the law; the latter were a sect who affected peculiar sanctity, and were regarded by the people as the most distinguished patterns of piety and virtue. The two were generally associated together in the Scriptures; because the Scribes, though not necessarily, yet, for the most part, belonged to the sect of the Pharisees: and, so united, they were considered as having all the learning and piety of the nation concentred in them. But, notwithstanding the high estimation in which they were held, our Lord most solemnly affirmed that none of them could, in their present state, be admitted into heaven; and that all who would be counted worthy of that honour, must attain a higher righteousness than theirs.This information, I say, is valuable; because, though it is not so definite as to encourage any to sit down contented with their attainments, it serves as a standard by which we may try our attainments, and a criterion whereby we may judge of our real state. (Read the entire sermon - Matthew 5:20 Evangelic And Pharisaic Righteousness Compared)

Righteousness (1343) (dikaiosune [word study] from dikaios [word study] = being proper or right in the sense of being fully justified being or in accordance with what God requires) is the quality of being upright. In its simplest sense dikaiosune conveys the idea of conformity to a standard or norm. In this sense righteousness is the opposite of hamartia (sin), which is defined as missing of the mark set by God. In this sense righteousness is the opposite of hamartia (sin), which is defined as missing of the mark set by God.

Dikaiosune is rightness of character before God and rightness of actions before men. Righteousness of God could be succinctly stated as all that God is, all that He commands, all that He demands, all that He approves, all that He provides through faith in Christ (Click here to read Pastor Ray Pritchard's interesting analysis of righteousness in the Gospel of Matthew).

Spurgeon comments that "The scribes and Pharisees were supposed to be righteous beyond all others. “Nay,” saith Christ; “you must go beyond them.” They were, after all, superficial, flimsy, pretentious, unreal in their righteousness; and we must have a far nobler character than they ever attained, or we “shall in no case enter into the kingdom of heaven.”

Dwight Pentecost has some helpful insights on this verse writing…

How good does a man have to be to go to heaven? No man is so depraved that he thinks bad people go to heaven. He instinctively recognizes that heaven is reserved for good people. So the question is not, Will bad people go to heaven? The question is, Just how good do good people have to be to go to heaven?… Pharisaism was a clever system devised to circumvent the requirements of the holiness of God and the demands of the Law. The Pharisees had the Law in their hand. They knew the revelation of the holiness of God revealed there. They knew the requirements of God as to the conduct of righteous men, but they realized they could not attain that standard. Therefore, they devised a system which essentially circumvented the requirements of the Law to make it possible for men to attain a substitute set of standards.

The Pharisees said that if one lived up to their interpretation of the Law, they would be acceptable to God. The Pharisees had codified the Scriptures into 365 negative commandments and 250 (Ed note: actually 248) positive commandments, and taught that if men kept all these, they would be acceptable in the sight of God. But every one of the commandments they had set before men had to do with external conduct. They were concerned only with external acts. They had interpreted the Law of God to apply only to outward acts, never to the thoughts that produced the act. They said it is wrong to murder a man, but said nothing about the hate that produces murder. They said it is wrong for a man to commit adultery, but nothing about the lust that produces adultery. They said it is wrong to steal, but said nothing about the covetousness which leads a man to steal. As long as a man was not caught in some act, he was righteous in the sight of the Pharisees. (Pentecost, J. D. Design for living: Lessons in Holiness from the Sermon on the Mount. Kregel Publications)

Surpasses (4052) (perisseuo from perissós = abundant) means to superabound, be in excess, to o overflow, to excel or to be in abundance. Perisseuo carries the idea of exceeding the requirements, of overflowing or overdoing. It means to exceed a fixed number of measure, to be left over and above a certain number or measure.

But whatever things were gain to me (as a Pharisee, a Hebrew of Hebrews, etc), those things I have counted as loss for the sake of Christ. More than that, I count all things to be loss in view of the surpassing value of knowing Christ Jesus my Lord, for whom I have suffered the loss of all things, and count them but rubbish in order that I may gain Christ, and may be found in Him, not having a righteousness of my own derived from the Law, but that which is through faithin Christ, the righteousness which comes from God on the basis of faith (see notes Philippians 3:7-8; 3:9)

Writing to the Romans Paul asks…

What shall we say then? That Gentiles, who did not pursue righteousness, attained righteousness, even the righteousness which is by faith; but Israel, pursuing a law of righteousness, did not arrive at that law. Why? Because they did not pursue it by faith, but as though it were by works. They stumbled over the stumbling stone, (see notesRomans 9:30; 9:31; 9:32)

Guzik illustrates just how fanatical the scribes and Pharisees were with a modern story…

The Pharisees were so scrupulous in their keeping of the law that they would even tithe from the small spices obtained from their herb gardens (Matthew 23:23). The heart of this devotion to God is shown by modern day Orthodox Jews. In early 1992, tenants let three apartments in an Orthodox neighborhood in Israel burn to the ground while they asked a rabbi whether a telephone call to the fire department on the Sabbath violated Jewish law. Observant Jews are forbidden to use the phone on the Sabbath, because doing so would break an electrical current, which is considered a form of work. In the half-hour it took the rabbi to decide "yes," the fire spread to two neighboring apartments. We can exceed their righteousness because our righteousness exceeds that of the scribes and Pharisees in kind, not degree. (Matthew 5)

MacDonald comments…

Jesus uses hyperbole (exaggeration) to drive home the truth that external righteousness without internal reality will not gain entrance into the kingdom. The only righteousness that God will accept is the perfection that He imputes to those who accept His Son as Savior (2 Cor. 5:21). Of course, where there is true faith in Christ, there will also be the practical righteousness that Jesus describes in the remainder of the Sermon. (MacDonald, W., & Farstad, A. Believer's Bible Commentary)

Scribes (1122) (grammateus from grapho = write) is literally a writer. A grammateus includes the ideas of scribe, secretary, and occasionally town-clerk (depending on the context). For the Jews a grammateus was a man learned in the Mosaic law and in sacred writings. In the Septuagint grammateus was frequently used for a political officer who assisted kings or magistrates by keeping written accounts of public acts and occurrences or royal revenues (2Ki 12:10). Their education made them indispensable in many civilizations, as they were needed to keep all military, government, legal, and financial records. The books of Ezra, Nehemiah, Daniel, Chronicles and Esther also indicate something of the beginnings of the movement, whereas Josephus and the NT speak of this group in a more advanced stage of development.

Ezra was referred to as a scribe…

"Ezra had set his heart to study the law of the LORD, and to practice it, and to teach His statutes and ordinances in Israel… Artaxerxes, king of kings, to Ezra the priest, the scribe of the law of the God of heaven, perfect peace. (Ezra 7:10,12)

Like Ezra the earliest scribes were found only among the priests and Levites. They recorded, studied, interpreted, and often taught Jewish law. Believing the Babylonian Captivity and Exile had come because of a lack of knowledge of and obedience to the Torah, the Law, the Israelite exiles devoted themselves to the study of the Old Testament. On them fell the duty of multiplying copies of the law and of teaching it to others (Ezra 7:6,10, 11, 12; Nehemiah 8:1,4,9,13)

The scribes became experts in and were considered authorities on the interpretation of the Scriptures during the Inter-testament Period. They preserved the law and were its defenders, especially in the Hellenistic period, when the priesthood had become corrupt. Scribes devoted themselves to the careful study of the text, and laid down rules for transcribing it with the most scrupulous precision. As time passed on the "words of the scribes" were honored above the Law. It was a greater crime to offend against them than against the Law.

Israel had two kinds of scribes, civil and ecclesiastical. The civil scribes functioned somewhat like notaries, and were involved in various governmental duties. Shimshai (Ezra 4:8) was such a scribe. The ecclesiastical scribes devoted their time to study of the Scriptures, and came to be its primary interpreters and articulators. As Jesus explained in Mt 5:21-48, despite their exposure to the Word of Truth, they missed the profound spiritual intent of the Word, specifically God's intent to change and effect our hearts. And they had fooled most of the populace who had a common saying that…

“If only two people go to heaven, one will be a scribe and the other a Pharisee.”

In view of this high regard that Jesus' audience doubtless had for the Scribes and Pharisees, one can imagine the shockwaves produced by His declaration that the only ones who would go to heaven were those whose righteousness greatly surpassed that of the Scribes and Pharisees!

Most of the scribes belonged to the party of the Pharisees, and were "professional students" and became the defenders and authorities regarding the Jewish law, both Scriptural and traditional. The Scribes were often referred to as lawyers because they were entrusted with the administration of the law as judges in the Sanhedrin (cf. Mt 22:35). They were a highly honored, prestigious group among the Jews, who recognized them as the key scholars of religious Judaism. The Scribes gathered around them pupils who they instructed in the Law and they expected their students to revere them beyond even what one would normally give to parents. The pupils were expected to retain the material taught and to transmit it without variation. Scribes were generally conservative and literal in regard to their interpretation of Scripture, but they were also generally legalistic and strict in regard to both the ceremonial (feasts, days, etc) and the moral law. Those of the scribes who were Sadducees were liberal in their interpretation of Scripture, not believing in such things as the resurrection and angels (Acts 23:8). Whether conservative or liberal, however, the scribes of Jesus’ day were alike in their opposition to Him.

Although scribes were the supposed experts in the Law, they like the Pharisees concerned themselves entirely with external observance of the law and tradition and paid little if any attention to heart motives or attitudes. The righteousness practiced by the scribes and Pharisees also fell short of God’s righteousness because it was partial, woefully incomplete. The righteousness practiced by the scribes and Pharisees also fell short of God’s righteousness because it was partial, woefully incomplete. In many ways the scribes and Pharisees were like liberal theologians of our day taking Scriptural terms and redefining them to suit their own human perspectives and philosophy. They reworked biblical teachings, commands, and standards to produce variations in keeping with their own desires and capabilities. They knew they could not be holy in the same way God is holy-and had no desire to be-so they simply changed the meaning of holiness. The righteousness of the scribes and Pharisees was completely self-centered, produced by their fleshly efforts for the purposes of self-glory. Their practices were designed to accomplish external, showy things about which they could boast and be proud. Their satisfaction came when they received approval and commendation from men not the approval of God!

Scribes in the time of our Lord Jesus, were the primary public teachers of the Jews and were esteemed as the interpreters of Scripture…

And gathering together all the chief priests and scribes of the people, he (King Herod) began to inquire of them where the Christ was to be born. And they said to him, "In Bethlehem of Judea, for so it has been written by the prophet, 6 'AND YOU, BETHLEHEM, LAND OF JUDAH, ARE BY NO MEANS LEAST AMONG THE LEADERS OF JUDAH; FOR OUT OF YOU SHALL COME FORTH A RULER, WHO WILL SHEPHERD MY PEOPLE ISRAEL'" Matthew 2:4, 5, 6

And His disciples asked Him, saying, "Why then do the scribes say that Elijah must come first?" Matthew 17:10

And Jesus answering began to say, as He taught in the temple, "How is it that the scribes say that the Christ is the son of David? Mark 12:35

Scribes wore long robes and loved pre-eminence

And in His teaching He was saying: "Beware of the scribes who like to walk around in long robes, and like respectful greetings in the market places, and chief seats in the synagogues, and places of honor at banquets, Mark 12:38,39

The manner of the scribes' teaching contrasted with that of Christ

for He was teaching them as one having authority, and not as their scribes. Matthew 7:29 (note); cf Mark 1:22

Scribes would seat themselves in the chair of Moses…

Then Jesus spoke to the multitudes and to His disciples, saying, "The scribes and the Pharisees have seated themselves in the chair of Moses (equivalent to a university’s “chair of philosophy.” To “sit in Moses’ seat” was to have the highest authority to instruct people in the law. Jesus is stressing the fact that this was an imaginary authority the scribes and Pharisees claimed for themselves. There was a legitimate sense in which the priests and Levites had authority to decide matters of the law (Dt 17:9), but the scribes and Pharisees had gone beyond any legitimate authority and were adding human tradition to the Word of God);

3 therefore all that they tell you, do and observe (as far as it was in accordance with the Word of God), but do not do according to their deeds; for they say things, and do not do them. 4 "And they tie up heavy loads (extra-biblical traditions, legalism), and lay them on men's shoulders; but they themselves are unwilling to move them with so much as a finger. 5 "But they do all their deeds to be noticed by men; for they broaden their phylacteries (to make them more prominent, even "super spiritual"!), and lengthen the tassels of their garments. 6 "And they love the place of honor at banquets, and the chief seats in the synagogues, 7 and respectful greetings in the market places, and being called by men, Rabbi (Jesus condemns not the title per se but the pride and pretense they associated with the title). Matthew 23:2-7

Scribes annulled the commandments of God for the sake of their own traditions.

(Jesus declared they were) thus invalidating the word of God by your tradition which you have handed down; and you do many things such as that." (Mark 7:13)

Scribes were condemned by Christ for hypocrisy

"Woe to you, scribes and Pharisees, hypocrites, because you travel about on sea and land to make one proselyte; and when he becomes one, you make him twice as much a son of hell as yourselves. Matthew 23:15

Scribes were frequently Pharisees and actually defended Paul

And there arose a great uproar; and some of the scribes of the Pharisaic party stood up and began to argue heatedly, saying, "We find nothing wrong with this man; suppose a spirit or an angel has spoken to him?" Acts 23:9

Scribes were often offended at out Lord’s conduct and teaching

But when the chief priests and the scribes saw the wonderful things that He had done, and the children who were crying out in the temple and saying, "Hosanna to the Son of David," they became indignant, 16 and said to Him, "Do You hear what these are saying?" And Jesus * said to them, "Yes; have you never read, 'OUT OF THE MOUTH OF INFANTS AND NURSING BABES THOU HAST PREPARED PRAISE FOR THYSELF'?" Matthew 21:15-16

5 And Jesus seeing their faith said to the paralytic, "My son, your sins are forgiven." 6 But there were some of the scribes sitting there and reasoning in their hearts, 7 "Why does this man speak that way? He is blaspheming; who can forgive sins but God alone?" 8 And immediately Jesus, aware in His spirit that they were reasoning that way within themselves, * said to them, "Why are you reasoning about these things in your hearts? Mark 2:6-8

16 And when the scribes of the Pharisees saw that He was eating with the sinners and tax-gatherers, they began saying to His disciples, "Why is He eating and drinking with tax-gatherers and sinners?" 17 And hearing this, Jesus * said to them, "it is not those who are healthy who need a physician, but those who are sick; I did not come to call the righteous, but sinners." Mark 2:16-17

And the scribes who came down from Jerusalem were saying, "He is possessed by Beelzebul," and "He casts out the demons by the ruler of the demons." And He called them to Himself and began speaking to them in parables, "How can Satan cast out Satan? (Mark 3:22-23)

Scribes tested the Jesus so that they might be able to accuse Him…

And the scribes and the Pharisees brought a woman caught in adultery, and having set her in the midst, 4 they said to Him, "Teacher, this woman has been caught in adultery, in the very act. 5 "Now in the Law Moses commanded us to stone such women; what then do You say?" 6 And they were saying this, testing Him, in order that they might have grounds for accusing Him. But Jesus stooped down, and with His finger wrote on the ground. John 8:3-6;

The Scribes were active in procuring our Lord’s death

From that time Jesus Christ began to show His disciples that He must go to Jerusalem, and suffer many things from the elders and chief priests and scribes, and be killed, and be raised up on the third day.

Now Herod was very glad when he saw Jesus; for he had wanted to see Him for a long time, because he had been hearing about Him and was hoping to see some sign performed by Him. 9 And he questioned Him at some length; but He answered him nothing. 10 And the chief priests and the scribes were standing there, accusing Him vehemently. Luke 23:8-10

Scribes opposed the disciples teaching about Jesus…

And it came about on the next day, that their rulers and elders and scribes were gathered together in Jerusalem; 6 and Annas the high priest was there, and Caiaphas and John and Alexander, and all who were of high-priestly descent. 7 And when they had placed them in the center, they began to inquire, "By what power, or in what name, have you done this?" Persecuted the Christians Acts 4:5-7; 6:12 ;

Pharisees (5330) (Pharisaios) is a word that is transliterated from the Hebrew. The Hebrew is apparently derived from parash which in turn is related to the Aramaic word peras signifying to separate, owing to a different manner of life from that of the general public.

The problem with the system of achieving acceptance with God is highlighted in Mark 7 in which Jesus warned His disciples against the doctrine of the Pharisees declaring that

IN VAIN DO THEY WORSHIP ME, TEACHING AS DOCTRINES THE PRECEPTS OF MEN.' "Neglecting the commandment of God, you hold to the tradition of men." He was also saying to them, "You nicely set aside the commandment of God in order to keep your tradition. "For Moses said, 'HONOR YOUR FATHER AND YOUR MOTHER'; and, 'HE WHO SPEAKS EVIL OF FATHER OR MOTHER, LET HIM BE PUT TO DEATH'; but you say, 'If a man says to his father or his mother, anything of mine you might have been helped by is Corban (that is to say, given to God),' 12 you no longer permit him to do anything for his father or his mother;13 thus invalidating the word of God by your tradition which you have handed down; and you do many things such as that." (Mark 7:7-13)

Barclay has some interesting historical details about the Pharisees writing that…

In many ways the Pharisees were the best people in the whole country. There were never more than 6,000 of them; they were what was known as a chaburah, or brotherhood. They entered into this brotherhood by taking a pledge in front of three witnesses that they would spend all their lives observing every detail of the scribal law. What exactly did that mean? To the Jew the Law was the most sacred thing in all the world. The Law was the first five books of the Old Testament. They believed it to be the perfect word of God. To add one word to it or to take one word away from it was a deadly sin. Now if the Law is the perfect and complete word of God, that must mean that it contained everything a man need know for the living of a good life, if not explicitly, then implicitly. The Law as it stood consisted of great, wide, noble principles which a man had to work out for himself. But for the later Jews that was not enough. They said: “The Law is complete; it contains everything necessary for the living of a good life; therefore in the Law there must be a regulation to govern every possible incident in every possible moment for every possible man.” So they set out to extract from the great principles of the law an infinite number of rules and regulations to govern every conceivable situation in life. In other words they changed the law of the great principles into the legalism of by-laws and regulations.

The best example of what they did is to be seen in the Sabbath law. In the Bible itself we are simply told that we must remember the Sabbath day to keep it holy and that on that day no work must be done, either by a man or by his servants or his animals. Not content with that, the later Jews spent hour after hour and generation after generation defining what work is and listing the things that may and may not be done on the Sabbath day. The Mishnah is the codified scribal law. The scribes spent their lives working out these rules and regulations. In the Mishnah the section on the Sabbath extends to no fewer than twenty-four chapters. The Talmud is the explanatory commentary on the Mishnah, and in the Jerusalem Talmud the section explaining the Sabbath law runs to sixty-four and a half columns; and in the Babylonian Talmud it runs to one hundred and fifty-six double folio pages. And we are told about a rabbi who spent two and a half years in studying one of the twenty-four chapters of the Mishnah.

The kind of thing they did was this. To tie a knot on the Sabbath was to work; but a knot had to be defined.

“The following are the knots the making of which renders a man guilty; the knot of camel drivers and that of sailors; and as one is guilty by reason of tying them, so also of untying them.”

On the other hand knots which could be tied or untied with one hand were quite legal. Further,

“a woman may tie up a slit in her shift and the strings of her cap and those of her girdle, the straps of shoes or sandals, of skins of wine and oil.”

Now see what happened. Suppose a man wished to let down a bucket into a well to draw water on the Sabbath day. He could not tie a rope to it, for a knot on a rope was illegal on the Sabbath; but he could tie it to a woman’s girdle and let it down, for a knot in a girdle was quite legal. That was the kind of thing which to the scribes and Pharisees was a matter of life and death; that was religion; that to them was pleasing and serving God.

Take the case of journeying on the Sabbath. Ex16:29 says:

“Remain every man of you in his place; let no man go out of his place on the seventh day.”

A Sabbath day’s journey was therefore limited to two thousand cubits, that is, one thousand yards. But, if a rope was tied across the end of a street, the whole street became one house and a man could go a thousand yards beyond the end of the street. Or, if a man deposited enough food for one meal on Friday evening at any given place, that place technically became his house and he could go a thousand yards beyond it on the Sabbath day. The rules and regulations and the evasions piled up by the hundred and the thousand.

Take the case of carrying a burden. Jeremiah 17:21, 22, 23, 24 said:

“Take heed for the sake of your lives and do not bear a burden on the Sabbath day.”

So a burden had to be defined. It was defined as

“food equal in weight to a dried fig, enough wine for mixing in a goblet, milk enough for one swallow, honey enough to put upon a wound, oil enough to anoint a small member, water enough to moisten an eye-salve,”

and so on and on. It had then to be settled whether or not on the Sabbath a woman could wear a brooch, a man could wear a wooden leg or dentures; or would it be carrying a burden to do so? Could a chair or even a child be lifted? And so on and on the discussions and the regulations went.

It was the scribes who worked out these regulations; it was the Pharisees who dedicated their lives to keeping them. Obviously, however misguided a man might be, he must be desperately in earnest if he proposed to undertake obedience to every one of the thousands of rules. That is precisely what the Pharisees did. The name Pharisee means the Separated One; and the Pharisees were those who had separated themselves from all ordinary life in order to keep every detail of the law of the scribes. (JohnCommentary - Daily Study Bible online).

You shall not enter - "Not" is the double negative (ou me) the strongest way to say "no" in Greek. In short, you won't enter because you have not been born again.

Spurgeon - These are solemn words of warning. God grant that we may have a righteousness which exceeds that of the scribes and Pharisees, a righteousness inwrought by the Spirit of God, a righteousness of the heart and of the life!

Near the end of His sermon, Jesus warned that…

Not everyone who says to Me, 'Lord, Lord,' will enter the kingdom of heaven; but he who does (present tense = habitually, not perfection but the general direction! The "pattern" of their life) the will of My Father who is in heaven. "Many will say to Me on that day, 'Lord, Lord, did we not prophesy in Your name, and in Your name cast out demons, and in Your name perform many miracles?' "And then I will declare to them, 'I never (not even at any time, never at all) knew you; DEPART FROM ME, YOU WHO PRACTICE (present tense = habitually) LAWLESSNESS.' (see notesMatthew 7:21; 7:22; 7:23)

In John Nicodemus a member of the Jewish ruling council, the Sanhedrin, commented on the fact that many knew He had come from God because of His signs. Jesus got right to the point and…

answered and said to him, "Truly, truly, I say to you, unless one is born again, he cannot see the kingdom of God (Heaven).." Nicodemus said to Him, "How can a man be born when he is old? He cannot enter a second time into his mother's womb and be born, can he?" Jesus answered, "Truly, truly, I say to you, unless one is born of water and the Spirit, he cannot enter into the kingdom of God (Heaven). (John 3:3-5)

Place yourself for a moment in Jesus' audience. You are a Jew and for years you have watched the Scribes and Pharisees meticulously keep the Law (or what you thought was the Law). And you knew that as it was said "if only two men are allowed to enter Heaven, then one will certainly be a teacher of the law and the other a Pharisee." No one else was even considered a viable candidate in comparison! The need to surpass the righteousness of the religious professionals would have come as a total shock.

In Mt 5:21-48, Jesus proceeds to illustrate what He meant by a surpassing righteousness, explaining that the righteousness of the Pharisees was only skin deep. Jesus begin to explain that God's righteousness called for true heart conformity to God's holy Law, not merely external and ceremonial but real and spiritual. Using six illustrations, Jesus explains what true righteousness from a new heart should look like.

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No Power (Ro 7:6-note) - I remember seeing a newspaper photograph of three signs nailed to a big oak tree. Their message was obvious. On the top sign were printed the words, "No Trespassing," on the middle one, "No Hunting," and on the bottom, "No Nothing."

The apostle Paul was very familiar with the urge behind such a response. In Romans 7 he pointed out that the law actually awakens rebellious desires within us (Ro 7:5-note). Being told not to do something excites our sinful nature to express itself.

Our rebellious response to negative rules points out our need for a strong, compelling motivation to do what's right. Paul said that we can go beyond a list of do's and don'ts to a love relationship with Christ Himself (Ro 7:6-note). The law carries with it the sentence of death because of our inability to keep it (Ro 7:10-note). But being united to Christ results in life.